EP0006538B1 - Acétals O,N-carbamoyl-triazolyl sulfénylés, leur préparation et leur utilisation comme fongicides - Google Patents

Acétals O,N-carbamoyl-triazolyl sulfénylés, leur préparation et leur utilisation comme fongicides Download PDF

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Publication number
EP0006538B1
EP0006538B1 EP79101939A EP79101939A EP0006538B1 EP 0006538 B1 EP0006538 B1 EP 0006538B1 EP 79101939 A EP79101939 A EP 79101939A EP 79101939 A EP79101939 A EP 79101939A EP 0006538 B1 EP0006538 B1 EP 0006538B1
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EP
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Prior art keywords
triazol
hydroxy
methyl
dimethyl
triazolyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
EP79101939A
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German (de)
English (en)
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EP0006538A1 (fr
Inventor
Wolfgang Dr. Krämer
Karl-Heinz Prof. Dr. Büchel
Engelbert Dr. Kühle
Paul-Ernst Dr. Frohberger
Wilhelm Dr. Brandes
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Bayer AG
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Bayer AG
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Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

Definitions

  • the present invention relates to new sulfenylated carbamoyl-triazolyl-O, N-acetals, a process for their preparation and their use as fungicides.
  • trityl-triazoles such as triphenyl- (1,2,4-triazol-1-yl) methane
  • acylated triazolyl-O, N-acetals such as 2-acyloxy-3,3-dimethyl-1-phenoxy-1- (1,2,4-triazol-1-yl) -butane, especially substituted in the phenyl part
  • the action of these compounds is not always entirely satisfactory, especially when low amounts and concentrations are used.
  • the compounds of formula (1) have two asymmetric carbon atoms; they can therefore be in the erythrow as well as in the threo form. In both cases, they are predominantly present as racemates.
  • the sulfenylated carbamoyl-triazolyl-O, N-acetals of the formula (I) obtainable according to the invention can be converted into the salts by reaction with acids, or the corresponding metal salt complexes can be obtained by reaction with metal salts.
  • the sulfenylated carbamoyl-triazolyl-O, N-acetals according to the invention have a considerably higher fungicidal activity, in particular against rust and mildew species. than the acylated triazolyl-O, N-acetals known from the prior art, which are chemically and functionally obvious compounds, and as the triphenyl- (1,2,4-triazol-1-yl) methane, which is a compound of the same type Direction of action is.
  • the substances according to the invention are therefore an enrichment of technology.
  • Formula (II) provides a general definition of the alcoholates of 2-hydroxy-1-phenoxy-1-triazolylbutanes to be used as starting materials.
  • M preferably represents the alkali metals lithium, sodium and potassium.
  • M also preferably represents the following quaternary ammonium groups: tetrabutylammonium, N-benzyl-N, N, N-trimethylammonium, hexadecyl-trimethyl-ammonium, 2-hydroxyethyl-trimethyl-ammonium, tetraethyl-ammonium, tetramethyl-ammonium, tetra-n-propylammonium , (Cyclopropylmethyl) trimethyl-ammonium, methyl-trioctyl-ammonium, N-phenyl-N, N, N-trimethyl-ammonium, N- (4-methylbenzyl) -N, N, N-trimethyl-ammonium, N-benzyl -N, N-
  • Formula (111) provides a general definition of the sulfenylated carbamoyl fluorides to be used as starting materials.
  • the compounds of the formula (111) are known (cf. DE-C-1 297 095 or US-A-3639471) or can be prepared by generally customary and known processes. You get it e.g. by reacting the corresponding carbamic acid fluorides with the corresponding sulfen chlorides.
  • Inert organic solvents are suitable as diluents for the reaction according to the invention. These preferably include ethers such as tetrahydrofuran and dioxane; Benzene; in some cases also chlorinated hydrocarbons, such as chloroform, methylene chloride or carbon tetrachloride.
  • reaction temperatures can be varied within a wide range. In general, between 20 and 150 ° C, preferably at the boiling point of the solvent, for example between 60 and 100 ° C.
  • the procedure is expediently started from a 2-hydroxy-3,3-dimethyl-1-phenoxy-1- (1,2,4-triazol-1-yl) butane derivative, the latter in a suitable inert organic solvent using alkali metal hydride or alkali metal amide in the alkali metal tall alcoholate of the formula (II) transferred, and the latter is immediately reacted with a carbamoyl fluoride of the formula (III) without isolation; the compounds of formula (I) according to the invention being obtained in one operation with the discharge of alkali metal fluorides.
  • reaction of the 2-hydroxy-3,3-dimethyl-1-phenoxy-1- (1,2,4-triazol-1-yl) butane derivative with the carbamoyl fluoride of the formula (III) carried out directly in the presence of potassium fluoride or 4-dimethylamino-pyridine as the base, and in the case of the pyridine as the base, this is added dropwise to the reaction mixture and is not initially introduced.
  • All physiologically acceptable acids are suitable for the preparation of acid addition salts of the compounds of the formula (I).
  • These preferably include the hydrohalic acids, e.g. hydrochloric acid and hydrobromic acid, especially hydrochloric acid, also phosphoric acid, nitric acid, sulfuric acid, mono- and bifunctional carboxylic acids and hydroxycarboxylic acids, e.g. Acetic acid, maleic acid, succinic acid, fumaric acid, tartaric acid, citric acid, salicylic acid, sorbic acid, lactic acid, as well as sulfonic acids, e.g. p-toluenesulfonic acid and 1,5-naphthalenedisulfonic acid.
  • hydrohalic acids e.g. hydrochloric acid and hydrobromic acid, especially hydrochloric acid, also phosphoric acid, nitric acid, sulfuric acid, mono- and bifunctional carboxylic acids and hydroxycarboxylic acids, e.g. Acetic acid, maleic
  • the salts of the compounds of formula (I) can be easily prepared by conventional salt formation methods, e.g. by dissolving a compound of formula (I) in a suitable inert solvent and adding the acid, e.g. Hydrochloric acid can be obtained and in a known manner, e.g. by filtration, isolated and, if necessary, cleaned by washing with an inert organic solvent.
  • a suitable inert solvent e.g. Hydrochloric acid
  • Hydrochloric acid can be obtained and in a known manner, e.g. by filtration, isolated and, if necessary, cleaned by washing with an inert organic solvent.
  • Anions of the salts are those which are derived from physiological acids. These preferably include the hydrohalic acids, e.g. hydrochloric acid and hydrobromic acid, as well as phosphoric acid, nitric acid and sulfuric acid.
  • the metal salt complexes of the compounds of formula (I) can in simpler. Can be obtained by conventional methods, e.g. by dissolving the metal salt in alcohol, e.g. Ethanol, and adding to the compound of formula (I). Metal salt complexes can be made in a known manner, e.g. by filtering, isolating and, if necessary, recrystallizing.
  • the active compounds according to the invention have a strong microbicidal action and can be used practically to combat unwanted microorganisms.
  • the active ingredients are suitable for use as pesticides.
  • Fungicidal agents in crop protection are used to control Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes. Ascomycetes, Basidiomycetes, Deuteromycetes.
  • the active compounds according to the invention can be used with particularly good success as crop protection agents to combat those fungi which cause real mildew diseases; to combat Podosphaera species, e.g. against the pathogen of apple mildew (Podosphaera leucotricha), of Erysiphe species, e.g. against the causative agent of cucumber mildew (Erysiphe cichoracearum) or barley powdery mildew or cereal powdery mildew (Erysiphe graminis); as well as to combat other cereal diseases, such as cereal rust.
  • the active compounds according to the invention not only have a protective effect, but are also partially systemically active. It is thus possible to protect plants against fungal attack if the active ingredient is supplied to the aerial parts of the plant via the soil and the roots or via the seeds.
  • the active ingredients can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, active ingredient-impregnated natural and synthetic substances, very fine encapsulations in polymeric substances and in coating compositions for seeds, and also in formulations with Fuel sets, such as smoking cartridges, cans, spirals. etc., as well as ULV cold and warm fog formulations.
  • customary formulations such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, active ingredient-impregnated natural and synthetic substances, very fine encapsulations in polymeric substances and in coating compositions for seeds, and also in formulations with Fuel sets, such as smoking cartridges, cans, spirals. etc., as well as ULV cold and warm fog formulations.
  • liquid solvents aromatics, such as xylene, toluene; or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylene or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, alcohols, such as butanol or glycol, and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or methyl isobutyl ketone , strongly polar solvents, such as dimethylformamide and dimethyl sulfoxide, and water;
  • Liquefied gaseous extenders or carriers mean those liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellant gas, such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide; Solid carriers are possible: for example
  • alkylaryl polyglycol ether alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates
  • Possible dispersants are: eg lignin sulfite waste liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, can be used in the formulations.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azole-metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can be present in the formulations or in the various use forms in a mixture with other known active compounds, such as fungicides, bactericides, insecticides.
  • active compounds such as fungicides, bactericides, insecticides.
  • the active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, emulsions, suspensions, powders, pastes and granules. They are used in the usual way, e.g. by pouring, dipping, spraying, spraying, atomizing, evaporating, injecting, 'slurrying, spreading, dusting, scattering, dry pickling, wet pickling, wet pickling, slurry pickling or incrusting.
  • the active compound concentrations in the use forms can be varied within a substantial range. They are generally between 1 and 0.000 1% by weight. preferably between 0.5 and 0.001%.
  • amounts of active ingredient of 0.001 to 50 g per kilogram of seed, preferably 0.01 to 10 g, are generally required.
  • active ingredient concentrations of 0.000 01 to 0.1% by weight, preferably 0.000 to 0.02%, are required at the site of action.
  • active compound 0.25 part by weight of active compound is taken up in 25 parts by weight of dimethylformamide and 0.06 part by weight of emulsifier (alkyl aryl polyglycol ether), and 975 parts by weight of water are added.
  • emulsifier alkyl aryl polyglycol ether
  • the single-leafed barley young plants of the Amsel variety are sprayed with the preparation of active compound as dewy. After drying, the young barley plants are dusted with spores from Erysiphe graminis var. Hordei.
  • the stocking of the plants with mildew pustules is evaluated.
  • the degree of infestation is expressed as a percentage of the infestation of the untreated control plants. 0% means no infection and 100% the same degree of infection as in the untreated control. The lower the mildew infestation, the more effective the active ingredient. Active substances, active substance concentrations in the spray mixture and degree of infestation are determined. In this test, e.g. the following compounds have a very good activity which is superior to that of the compounds known from the prior art: compounds according to Preparation Examples 2, 3, 4 and 1.
  • Barley powdery mildew test (Erysiphe greminis var. Hordei) / systemic (fungal cereal sprout disease).
  • the active ingredients are used as powdered seed treatment agents. They are made by. Strain the respective active ingredient with a mixture of equal parts by weight of talc and kieselguhr to a fine powdery mixture with the desired active ingredient concentration.
  • the degree of infestation is expressed as a percentage of the infestation of the untreated control plants. 0% means no infection and 100% the same degree of infection as in the untreated control. The lower the mildew infestation, the more effective the active ingredient.
  • active compound 0.25 part by weight of active compound is taken up in 25 parts by weight of dimethylformamide and 0.06 part by weight of alkyl aryl polyglycol ether, and 975 parts by weight of water are added.
  • the concentrate is diluted with water to the desired final concentration of the spray mixture.
  • the stocking of the plants with rust pustules is evaluated.
  • the degree of infestation is expressed as a percentage of the infestation of the untreated control plants. 0% means no infection and 100% the same degree of infection as in the untreated control. The less active the rust, the more effective the active ingredient.
  • Solvent 4.7 parts by weight of acetone.
  • Emulsifier 0.3 part by weight of alkyl aryl polyglycol ether.
  • the amount of active ingredient required for the desired active ingredient concentration in the spray liquid is mixed with the stated amount of solvent and the concentrate is diluted with the stated amount of water which contains the additives mentioned.
  • the spray liquid is used to spray young cucumber plants with about three leaves to the point of dripping wet.
  • the cucumber plants remain in the greenhouse for drying for 24 hours. Then they are dusted with conidia of the fungus Erysiphe cichoracearum for inoculation. The plants are then placed in a greenhouse at 23-24 ° C. and at a relative humidity of approx. 75%.
  • Solvent 4.7 parts by weight of acetone.
  • Emulsifier 0.3 part by weight of alkyl aryl polyglycol ether.
  • the amount of active ingredient of the solvent required for the desired active ingredient concentration in the spray liquid is mixed and the concentrate is diluted with the stated amount of water which contains the additives mentioned.
  • the spray liquid is used to spray young apple seedlings that are in the 4 to 6 leaf stage until dripping wet.
  • the plants remain in the greenhouse for 24 hours at 20 ° C and a relative humidity of 70%. Then they are inoculated by dusting with conidia of the powdery mildew pathogen (Podosphaera leucotricha) and placed in a greenhouse with a temperature of 21 to 23 ° C and a relative humidity of approx. 70%.
  • the infestation of the seedlings is determined 10 days after the inoculation.
  • the rating values received are converted into percent infestation. 0% means no infection, 100% means that the plants are completely infected.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Claims (4)

1. Carbamoyl-triazolyl-O,N-acétals sulfénylés de formule générale 1
Figure imgb0021
dans laquelle
R1 représente un méthyl ou un phényle éventuellement substitué par du chlore ou méthyle,
R2 représente trifluorométhyle, chlorodifluorométhyle, dichlorofluorométhyle et trichlorométhyle,
X et Y représentent de l'hydrogène, du fluor, du chlore ou du brome,
Z représente du fluor, chlore, brome, méthyle, éthyle de même qu'un phényle éventuellement substitué par du chlore ou méthyle et
n représente les nombres 0, 1 ou 2,

leurs sels d'addition d'acides physiologiquement compatibles et complexes de sels métalliques.
2. Procédé de fabrication des carbamoyl-triazolyl-O,N-acétals sulfénylés selon la revendication 1, caractérisé en ce qu'on fait réagir un alcoolate d'un 2-hydroxy-1-phénoxy-1-triazolyl-butane de formule Il
Figure imgb0022
dans laquelle
X, Y, Z et n ont la signification indiquée à la revendication 1 et
M représente un métal alcalin, un groupe ammonium ou phosphonium quaternaire, avec un fluorure de carbamoyle sulfénylé de formule III
Figure imgb0023
dans laquelle
R1 et R2 ont la signification indiquée à la revendication 1,

en présence d'un diluant, et en ce qu'en outre, éventuellement, on convertit les carbamoyl-triazolyl-O,N-acétals sulfénylés obtenus de formule (I), par réaction avec des acides, en leurs sels, ou, par réaction avec des sels métalliques, en les complexes de sels métalliques correspondants.
3. Agents fongicides, caractérisés par une teneur en au moins un carbamoyl-triazolyl-O,N-acétal sulfénylé selon la revendication 1.
4. Utilisation des carbamoyl-triazolyl-O,N-acétals sulfénylés selon la revendication 1 pour combattre les champignons.
EP79101939A 1978-06-26 1979-06-15 Acétals O,N-carbamoyl-triazolyl sulfénylés, leur préparation et leur utilisation comme fongicides Expired EP0006538B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19782827968 DE2827968A1 (de) 1978-06-26 1978-06-26 Sulfenylierte carbamoyl-triazolyl- o,n-acetale, verfahren zu ihrer herstellung und ihre verwendung als fungizide
DE2827968 1978-06-26

Publications (2)

Publication Number Publication Date
EP0006538A1 EP0006538A1 (fr) 1980-01-09
EP0006538B1 true EP0006538B1 (fr) 1981-12-02

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EP79101939A Expired EP0006538B1 (fr) 1978-06-26 1979-06-15 Acétals O,N-carbamoyl-triazolyl sulfénylés, leur préparation et leur utilisation comme fongicides

Country Status (10)

Country Link
US (1) US4239766A (fr)
EP (1) EP0006538B1 (fr)
JP (1) JPS554395A (fr)
BR (1) BR7903977A (fr)
CS (1) CS215022B2 (fr)
DD (1) DD144353A5 (fr)
DE (2) DE2827968A1 (fr)
DK (1) DK267279A (fr)
IL (1) IL57626A0 (fr)
PL (1) PL115641B1 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2918894A1 (de) * 1979-05-10 1980-11-20 Bayer Ag Fluorierte 1-triazolyl-butan-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide
DE2918896A1 (de) * 1979-05-10 1980-11-20 Bayer Ag Antimikrobielle mittel
DE2938534A1 (de) * 1979-09-24 1981-04-23 Bayer Ag, 5090 Leverkusen Acylierte triazolyl-(gamma)-fluorpinakolyl-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide
DE2938575A1 (de) * 1979-09-24 1981-04-23 Bayer Ag, 5090 Leverkusen Acylierte imidazolyl-(gamma)-fluorpinakolyl-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide
DE3033592A1 (de) * 1980-09-06 1982-04-22 Bayer Ag, 5090 Leverkusen Fluorierte 1-azolyl-butan-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide
DE3315262A1 (de) * 1983-04-27 1984-10-31 Bayer Ag, 5090 Leverkusen Carbamoylierte azolylalkyl-phenoxy-carbinole, verfahren zu ihrer herstellung sowie ihre verwendung als pflanzenschutzmittel

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AT214703B (de) * 1948-05-18 Exxon Research Engineering Co Verfahren zur Bekämpfung von Schädlingen
US2553775A (en) * 1949-06-21 1951-05-22 Standard Oil Dev Co N-thiotrichloromethyl amides and parasiticidal compositions containing them
FR1310083A (fr) * 1960-11-03 1963-03-04
DE2600799A1 (de) * 1976-01-10 1977-07-14 Bayer Ag Acylierte triazolyl-0,n-acetale, verfahren zu ihrer herstellung und ihre verwendung als fungizide
DE2635883A1 (de) * 1976-08-10 1978-02-16 Bayer Ag N-sulfenylierte oximcarbamate, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und nematozide
DE2635663A1 (de) * 1976-08-07 1978-02-09 Bayer Ag Azolyl-carbonsaeure-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide
DE2720949A1 (de) * 1977-05-10 1978-11-23 Bayer Ag Azolylaether-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide

Also Published As

Publication number Publication date
JPS554395A (en) 1980-01-12
PL115641B1 (en) 1981-04-30
US4239766A (en) 1980-12-16
DK267279A (da) 1979-12-27
CS215022B2 (en) 1982-06-25
IL57626A0 (en) 1979-10-31
PL216553A1 (fr) 1980-03-10
EP0006538A1 (fr) 1980-01-09
BR7903977A (pt) 1980-03-11
DE2961504D1 (en) 1982-01-28
DD144353A5 (de) 1980-10-15
DE2827968A1 (de) 1980-01-10

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